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693057 Aldrich

(S)-BINAP

Synonym: (S)-(−)-(1,1′-Binaphthalene-2,2′-diyl)bis(diphenylphosphine), (S)-(−)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene, (S)-(−)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl, (S)-(−)-BINAP

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Properties

Related Categories Asymmetric Synthesis, BINAPs, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Privileged Ligands and Complexes More...
optical activity   [α]20/D -222, c = 0.5 in benzene
mp   238-240 °C(lit.)

Description

Packaging

100, 500 mg in glass bottle

Legal Information

Sold in collaboration with Takasago for research purposes only.

Application

Takasago Ligands and Complexes for Asymmetric Reactions

Reactant involved in:
• Enantioselective and diastereoselective unpoled carbonyl allylation
• Syntehsis of organophophine oxides as anittumor agents
• SN2 halogenation of hydroxy groups
• Synthesis of BINAP complexes
• Studies of conformational flexibility of BINAP chelates

Price and Availability

Safety & Documentation

Safety Information

WGK Germany 
3

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Articles

BINAP/SEGPHOS® Ligands and Complexes

Since the development of BINAP by Noyori 20 years ago, extensive research has been accomplished using this chiral ligand. BINAP proved to be one of the most versatile ligands, catalyzing a wide range...
William Sommer and Daniel Weibel
Aldrich ChemFiles 2008, 8.2, 3.
Keywords: Addition reactions, Aminations, Arylations, Asymmetric synthesis, Building blocks, Catalysis, Cyclizations, Epoxidations, Hydrogenations, Hydrosilylations, Ligands, Reductive aminations, Sharpless Epoxidation, transformation

Takasago Ligands and Complexes for Asymmetric Reactions

The quest to find chiral catalysts capable of achieving high enantiomeric excess for a variety of asymmetric transformations has been an ongoing endeavor for the past 40 years. One of the most releva...
Keywords: Addition reactions, Arylations, Asymmetric synthesis, Catalysis, Hydrogenations, Ligands, transformation

Related Content

Takasago Ligands and Complexes for Asymmetric Reactions

Introduction The quest to find chiral catalysts capable of achieving high enantiomeric excess for a variety of asymmetric transformations has been an ongoing endeavor for the past 40 years. One of th...
Keywords: Addition reactions, Applications, Arylations, Asymmetric synthesis, Building blocks, Catalysis, Epoxidations, Hydrogenations, Hydrosilylations, Ligands, Sharpless Epoxidation, transformation

Peer-Reviewed Papers

References

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The preparation of bi-functional organophosphine oxides as potential antitumor agents K. Lam, et al., Eur. J. Med. Chem. 45, 5527-5530, (2011)

Halogenative kinetic resolution of ß-aryloxy cyclic alcohols: chiral BINAP-mediated SN2 displacement of hydroxy groups by chlorides with inversion of stereochemistry E. A. Jaseer, et al., Tetrahedron Asymmetry 21, 2177-2182, (2010)

BINAP: rhodium-diolefin complexes in asymmetric hydrogenation A. Preetz, et al., Tetrahedron Asymmetry 21, 1226-1231, (2010)

Asymmetric catalysis with 7-ring chelate diphosphines: DIOP, BINAP and conformational mobility J. A. Raskatov, et al., Tetrahedron Asymmetry 21, 1737-1744, (2010)

BINAP-AgSbF6 vs. BINAP-AgClO4 complexes as catalysts for the enantioselective 1,3-dipolar cycloaddition of azomethine ylides and alkenes M. Martin-Rodriguez, et al., Synlett 6, 962-966, (2010)

Polarity Inversion of Donor-Acceptor Cyclopropanes: Disubstituted d-Lactones via Enantioselective Iridium Catalysis J. Moran, et al., J. Am. Chem. Soc. 133, 18618-18621, (2011)

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The preparation of bi-functional organophosphine oxides as potential antitumor agents. Kim-Hung Lam et al Eur. J. Med. Chem. 45, 5527-30, (2010)

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Merck 14,1223

Fieser 10,36 / Fieser 11,53 / Fieser 12,56 / Fieser 13,36 / Fieser 14,38 / Fieser 15,34 / Fieser 16,32 / Fieser 17,36

FT-IR 2 (2), 3323:C / FT-NMR 1 (2), 1663:C / RegBook 1 (2), 2267:N / Structure Index 1, 355:C:4

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